EP1316436A1 - Optisches informationsaufzeichnungsmedium - Google Patents

Optisches informationsaufzeichnungsmedium Download PDF

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Publication number
EP1316436A1
EP1316436A1 EP01958393A EP01958393A EP1316436A1 EP 1316436 A1 EP1316436 A1 EP 1316436A1 EP 01958393 A EP01958393 A EP 01958393A EP 01958393 A EP01958393 A EP 01958393A EP 1316436 A1 EP1316436 A1 EP 1316436A1
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EP
European Patent Office
Prior art keywords
group
substituted
unsubstituted
layer
recording
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01958393A
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English (en)
French (fr)
Inventor
Ryousuke Nara
Yoshiteru Taniguchi
Norihiko Mihara
Tadashi Koike
Atsuhiro Osuka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsui Chemicals Inc
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Mitsui Chemicals Inc
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Filing date
Publication date
Application filed by Mitsui Chemicals Inc filed Critical Mitsui Chemicals Inc
Publication of EP1316436A1 publication Critical patent/EP1316436A1/de
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/248—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes porphines; azaporphines, e.g. phthalocyanines

Definitions

  • the present invention relates to an optical information recording medium, particularly an optical information recording medium of recordable type capable of conducting recording and reproduction using a red and/or blue laser.
  • CD-R compact disc of recordable type
  • DVD-R digital versatile disc
  • an organic dye is used in a recording layer; and the dye, when irradiated with a laser beam, is heated locally at the irradiated portion of the recording layer and causes chemical or physical changes such as decomposition, vaporization, melting-solidification and the like, whereby pits are formed and information recording is made possible.
  • the organic dye used in the recording layer is required to have a high reflectance before recording so as to give a large modulation factor; therefore, the organic dye is desired to have an absorption peak of large absorption coefficient at about a reproduction wavelength and a high refractive index.
  • cyanine dyes As an organic dye having a high absorption coefficient and a high refractive index, cyanine dyes are mentioned. However, these cyanine dyes are known to generate singlet state oxygen owing to the self-sensitization and easily undergo photo-deterioration. Hence, a metal complex typified by nickel-dithiolate complex has often been mixed, as an oxygen quencher, into the cyanine dye; this has given improved light resistance but has incurred lower recording characteristic and a higher cost. Therefore, the dye used in the recording layer is desired to have by itself both light resistance and a high refractive index.
  • the present inventors made a study in order to solve the above problems. As a result, the present inventors found out that when an extended porphyrin compound is used in the recording layer of an optical recording medium, the compound shows both good light resistance and a high refractive index. The present invention has been completed based on the above finding.
  • the present invention lies in the followings.
  • the heterocyclic rings possessed by the extended porphyrin compound contained in the recording layer, desirably have substituents introduced for improvements in solubility, coatability and durability.
  • the heterocyclic rings may not have substituents.
  • halogens such as fluorine, chlorine, bromine and iodine
  • hydroxyl group mercapto group
  • nitro group cyano group
  • amino group sulfonic acid group
  • unsubstituted alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, nonyl, decyl, dodecyl and cyclohexyl
  • substituted alkyl groups such as methylcyclohexyl, ethynyl, propenyl and benzyl
  • aryl groups such as phenyl, toluyl and x
  • methylsulfonic acid or benzenesulfonic acid) ester groups ; carboxylic acid amide groups such as ethylaminocarboxy and phenylaminocarboxy; sulfonamide groups such as ethylsulfonamide, phenylsulfonamide and benzylsulfonamide; carbonyl groups such as acetyl, ethylcarbonyl, butylcarbonyl and phenylcarbonyl; silyl groups such as trimethylsilyl, triethylsilyl, tripropylsilyl, tributylsilyl and triphenylsilyl; siloxy groups such as trimethoxysilyl; and so forth.
  • carboxylic acid amide groups such as ethylaminocarboxy and phenylaminocarboxy
  • sulfonamide groups such as ethylsulfonamide, phenylsulfonamide
  • the substituents are not restricted thereto.
  • the substituents also include those substituents in which other substituent is added to some of the above-mentioned substituents, for example, halogenated alkyls, halogenated aryls, hydroxyalkyls and hydroxyaryls.
  • adjacent substituents for example, two substituents on a pyrrole ring, or a substituent on a pyrrole ring and a substituent on a methine group connecting two pyrrole rings, may bond to each other to form a new ring.
  • Such an extended porphyrin compound can be obtained by subjecting a substituted or unsubstituted pyrrole and an appropriate aldehyde to a condensation reaction using, for example, the method described in a literature "M. Neves et al., Chem. Comm., 1999, p. 385". (wherein Ra, Rb and Rc have the same definitions as given for R 1 to R 15 , and n is an integer of 1 or more).
  • introduction of different substituents into each pyrrole ring and meso position can be performed by conducting a reaction using a plurality of pyrroles and/or a plurality of aldehydes.
  • the conformation of the extended porphyrin may be any of a state in which each pyrrole nitrogen is directed to the inside of the porphyrin ring and each meso position substituent is directed to the outside of the porphyrin ring as shown in formula (1), and a state in which each pyrrole nitrogen is directed to the outside of the porphyrin ring and each meso position substituent is directed to the inside of the porphyrin ring.
  • the position of NH proton may be at any pyrrole nitrogen of the porphyrin ring owing to conjugation.
  • the extended porphyrin represented by the general formula (1), used in the present invention may be in a neutral state or may form, as a bivalent anion, a complex with one or more metals or with one or more metal compounds.
  • the metals there are mentioned Zn, Mg, Ca, Sr, Ba, Sc, Y, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Ti, Zr, Hf, V, Nb, Ta, Th, U, Cr, Mo, W, Mn, Tc, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag, Au, Cd, Hg, Al, Ga, In, Tl, Si, Ge, Sn, Pb, Sb, Bi, etc.
  • the metals may each coordinate to one or more pyrrole nitrogens of the extended porphyrin ring; further, other atom (e.g. halogen) or atomic group
  • a single-substrate type ordinarily consists of a transparent substrate, a recording layer, a metal reflecting layer and a protective layer, and may further have a foundation layer and a protective layer for improved properties.
  • the substrate used in the present invention may be any transparent material because recording and reproduction are conducted optically.
  • organic polymer materials such as polycarbonate, polyacrylate, polymethacrylate, polystyrene, polyvinyl chloride, polyester, polyolefin, epoxy resin and the like; and inorganic materials such as glass and the like.
  • a polycarbonate resin which is well balanced between light transmittance and heat resistance and allows easy molding, is preferred particularly.
  • a polyolefin having a cyclic skeleton is also desirable because it has low anisotropy and shows low water absorption.
  • the substrate may have, on the surface, guide grooves or pits indicating recording positions, or some of the pits for information, etc. exclusively used for reproduction.
  • These grooves, pits, etc. are ordinarily formed at the time of substrate production conducted by injection molding or casting, but may be formed by a laser cutting method or a photo-polymer method.
  • the recording layer of the optical information recording medium of the present invention contains a compound represented by the general formula (1), and can conduct recording by applying a laser beam thereto to decompose the compound to form pits.
  • a compound represented by the general formula (1) In the recording layer, one or more kinds of other dyes may be mixed into the dye represented by the general formula (1).
  • light-non-absorbing substances may be added to the dye represented by the general formula (1) or its mixture with other dye(s) for improved recording characteristic and durability.
  • the dyes other than the dye represented by the general formula (1), used in the recording layer are large ring azaanulene dyes (for example, phthalocyanine dyes, naphthalocyanine dyes and azaporphyrin dyes having 1 to 4 meso-position nitrogen atoms); polymethine dyes (for example, cyanine dyes, merocyanine dyes, and squarylium dyes); anthraquinone dyes; azulenium dyes; azo dyes; and indoaniline dyes.
  • phthalocyanine dyes having high durability and light resistance are desired particularly.
  • the dye-containing recording layer may be a laminated layer consisting of two or more layers.
  • the dye represented by the general formula (1) may be used only in one layer or in two or more layers.
  • the recording layer in a laminated structure consisting of two or more layers and allows one of the layers to contain a dye represented by the general formula (1) and other layer(s) to contain a dye(s) other than the dye represented by the general formula (1) so as to allow for multi-wavelength recording.
  • the dye(s) used in the recording layer(s) other than the layer containing the dye represented by the general formula (1) there are mentioned large ring azaanulene dyes (for example, phthalocyanine dyes, naphthalocyanine dyes and azaporphyrin dyes having 1 to 4 meso-position nitrogen atoms); polymethine dyes (for example, cyanine dyes, merocyanine dyes, and squarylium dyes); anthraquinone dyes; azulenium dyes; azo dyes; indoaniline dyes; and so forth.
  • a dye(s) different in optical characteristic from the dye of the general formula (1) is (are) selected.
  • the recording layer containing such a dye(s) can be formed ordinarily by spin coating, spray coating, dip coating, roll coating, etc.
  • substances constituting the recording layer such as dye, resinous binder and the like are dissolved in a solvent giving no damage to the substrate used, to prepare a coating solution; and the solution is coated on the substrate and dried to form a recording layer.
  • the solvent there are preferably used aliphatic or alicyclic hydrocarbons such as hexane, heptane, octane, decane and cyclohexane; aromatic hydrocarbons such as toluene and xylene; ethers such as diethyl ether, dibutyl ether and tetrahydrofuran; alcohols such as methanol, ethanol, isopropanol, tetrafluoropropanol and methyl cellosolve; halogen compounds such as chloroform, dichloromethane and 1,2-dichloroethane; and so forth. These solvents may be used singly or in admixture of two or more kinds. When the recording layer is formed in a laminated structure consisting of two or more layers, it is desired to use a solvent which does not adversely affect the layer formed earlier.
  • the recording layer may also be formed by vacuum deposition. This method is effective when the substances to constitute the recording layer have low solubility in solvents or when it is impossible to select a solvent which gives no damage to the substrate used.
  • the recording layer has a thickness of 10 to 300 nm, preferably 50 to 200 nm.
  • a foundation layer may be formed between the substrate and the recording layer for the purposes of, for example, prevention of recording layer from deterioration. It is possible to use, for example, a layer composed of an organic material (e.g. a polystyrene or a polymethacrylate) or an inorganic material (e.g. SiO 2 ). These materials may be used singly or in admixture of two or more kinds of organic materials or two or more kinds of inorganic materials.
  • an organic material e.g. a polystyrene or a polymethacrylate
  • an inorganic material e.g. SiO 2
  • two or more kinds of these materials may be used in laminated layers; that is, laminated layers each containing a different organic material, laminated layers each containing a different inorganic material, or laminated layers consisting of a layer containing an organic material and a layer containing an inorganic material may be formed.
  • a reflecting layer using a metal such as Au, Al, Pt, Ag and Ni, or an alloy thereof.
  • Au is desirable because it is stable to oxygen and water.
  • a reflecting layer is formed by vapor deposition, sputtering, ion plating, etc.
  • the reflecting layer has a thickness of 10 to 300 nm, desirably 30 to 150 nm.
  • the reflecting layer is formed at a side opposite to the side of light incidence; therefore, when light incidence is made from the protective layer or dummy substrate (both described later) side, the reflecting layer is formed at the substrate side relative to the recording layer.
  • an intermediate layer may be formed in order to achieve, for example, an increased adhesivity or an increased reflectance.
  • a protective layer may be formed on the reflecting layer or the recording layer.
  • the protective layer there is no particular restriction as to the protective layer as long as the layer protects the reflecting layer or the recording layer from an external force.
  • polymer materials such as acrylate or methacrylate polymer obtained by general radical polymerization or epoxy polymer obtained by photo-induced cationic polymerization. These polymer materials may be obtained by homopolymerization or copolymerization with other monomer, oligomer or the like. These materials may also be diluted with a solvent and coated.
  • ultraviolet curing resins for example, acrylate resins such as urethane acrylate, epoxy acrylate and polyester acrylate are desired for the workability.
  • the protective layer is formed by spin coating, dip coating, bar coating, screen printing, etc. Spin coating is employed in many cases for the workability.
  • the protective layer has a thickness of generally 1 to 100 ⁇ m. In the present invention, a thickness of 1 to 20 ⁇ m is preferred.
  • the thus-formed protective layer protects the recording layer or the reflecting layer.
  • a strong protective layer is required depending upon the use condition of the resulting recording medium, it is possible to form an inorganic or organic protective layer on the protective layer made of the above-mentioned polymer material.
  • the inorganic protective layer there are mentioned SiO 2 , Si 3 N 4 , MgF 2 , AlN, SnO 2 , etc.
  • the organic protective layer there are mentioned a thermosetting resin, an electron beam curing resin, an ultraviolet curing resin, etc.
  • the thermosetting resin is dissolved in an appropriate solvent to prepare a coating fluid, followed by coating of the fluid and subsequent drying and curing.
  • an organic protective layer is formed using an ultraviolet-curing resin
  • a coating fluid is prepared from the ultraviolet-curing resin per se or by dissolving the resin in an appropriate solvent, the coating fluid is coated, and an ultraviolet light is applied to cure the resin.
  • An inorganic protective layer can be formed by vapor deposition, etc. These materials may be used singly or in admixture.
  • the protective layer may be formed not only in a single layer but also in a plurality of layers for increased adhesivity with other layer and other purpose.
  • a substrate having a recording layer formed thereon may be laminated with another substrate.
  • the another substrate may be a dummy substrate having no layer (e.g. recording layer) formed thereon; or, a substrate having a recording layer formed thereon may be laminated with another substrate having a recording layer, a reflecting layer, etc. formed thereon, in such a state that the sides of the two substrates having respective recording layers face each other.
  • the adhesion method employed in this case there are mentioned, for example, a hot melt method, a method using an ultraviolet curing adhesive, and a method using a one-pack or two-pack type reactive adhesive.
  • hexaphyrin of formula (E) was dissolved in chloroform so as to give a concentration of 10 g/l.
  • the resulting solution was coated on a glass chip by spin coating, to form a film of 120 nm in thickness.
  • the thin film was measured for UV spectrum. The UV spectrum is shown in Fig. 1.
  • the hexaphyrin of formula (E) was vapor-deposited on a glass substrate-in 8 different thicknesses between 45 nm and 120 nm, to prepare samples. Each sample was measured for absorption spectrum and reflection spectrum, from which refractive indexes and extinction coefficients at various wavelengths were calculated.
  • the dye of formula (E) was coated on a polycarbonate substrate by spin coating, then exposed to a light from a carbon arc, and measured for UV spectrum. A ratio of ⁇ max absorbance after light exposure to ⁇ max absorbance before light exposure was determined and taken as retention. A high retention of 99% was obtained after 40 hours of a light exposure test.
  • Fig. 1 is shown the thin-film spectrum after the light durability test, together with that before the test.
  • a film (thickness: about 80 nm) of the dye of formula (E) was formed, by vapor deposition, on a polycarbonate substrate of 0.6 mm in thickness and 120 mm in diameter (pitch between grooves: 0.74 ⁇ m, groove width: 0.3 ⁇ m, groove depth: 100 nm). Thereon was formed an Au layer in a thickness of 80 nm by sputtering, and further SD-17 of UV-curing type was laminated. Thereon was laminated a dummy substrate of 0.6 mm in thickness, made of a polycarbonate, whereby a trial optical recording medium was produced.
  • a dye of the formula (G) was dissolved in cyclohexane so as to give a concentration of 10 g/l.
  • the resulting solution was coated, by spin coating, on a polycarbonate substrate of 0.6 mm in thickness and 120 mm in diameter (pitch between grooves: 0.74 m, groove width: 0.3 ⁇ m, groove depth: 100 nm) to form a film of about 60 nm in thickness.
  • an Au reflecting layer in a thickness of 80 nm by sputtering, and further SD-17 of UV-curing type was laminated.
  • the extended porphyrin of the general formula (1) used in the present invention as a recording layer dye has by itself durability against light, a high refractive index and an appropriate extinction coefficient; therefore, the present invention can provide an optical information recording medium having good recording characteristic and excellent light durability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
EP01958393A 2000-08-23 2001-08-22 Optisches informationsaufzeichnungsmedium Withdrawn EP1316436A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2000252323 2000-08-23
JP2000252323 2000-08-23
PCT/JP2001/007178 WO2002016144A1 (fr) 2000-08-23 2001-08-22 Support optique d'enregistrement de donnees

Publications (1)

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EP1316436A1 true EP1316436A1 (de) 2003-06-04

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EP01958393A Withdrawn EP1316436A1 (de) 2000-08-23 2001-08-22 Optisches informationsaufzeichnungsmedium

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US (1) US20030118937A1 (de)
EP (1) EP1316436A1 (de)
TW (1) TW544674B (de)
WO (1) WO2002016144A1 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006015714A1 (de) * 2004-08-06 2006-02-16 Lanxess Deutschland Gmbh Optische datenträger enthaltend porphyrinsulfonamide in der informationsschicht
ITUD20130075A1 (it) * 2013-05-27 2014-11-28 Univ Degli Studi Udine Nuove pentafirine

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4282292B2 (ja) * 2002-09-10 2009-06-17 独立行政法人科学技術振興機構 ヘキサン可溶性ヘキサフィリン
JP2004160742A (ja) * 2002-11-11 2004-06-10 Tdk Corp 光記録ディスクおよびその製造方法ならびに光記録ディスクの光記録再生方法
TWI675907B (zh) 2015-01-21 2019-11-01 日商Ｊｓｒ股份有限公司 固體攝像裝置
JP2016162946A (ja) * 2015-03-04 2016-09-05 Jsr株式会社 固体撮像装置
CN107037096B (zh) * 2017-04-01 2019-04-16 南京师范大学 一种基于CoCuCdTCPP配位聚合物修饰的电化学传感器及其制备方法和应用
CN112047821B (zh) * 2020-08-05 2022-05-03 中山大学 一种甲乙酮的制备方法

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US5159065A (en) * 1989-12-21 1992-10-27 Board Of Regents, The University Of Texas System Sapphyrins, derivatives and syntheses
US5486437A (en) * 1993-04-08 1996-01-23 Sony Corporation Optical recording method
US5658707A (en) * 1994-10-18 1997-08-19 Mitsui Toatsu Chemicals, Inc. Optical recording media
US5883246A (en) * 1996-03-07 1999-03-16 Qlt Phototherapeutics, Inc. Synthesis of polypyrrolic macrocycles from meso-substituted tripyrrane compounds
JPH11138993A (ja) * 1997-11-11 1999-05-25 Matsushita Electric Ind Co Ltd 光記録媒体及び光記録再生方法
JP3685368B2 (ja) * 1998-08-18 2005-08-17 株式会社リコー 光記録媒体

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See references of WO0216144A1 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006015714A1 (de) * 2004-08-06 2006-02-16 Lanxess Deutschland Gmbh Optische datenträger enthaltend porphyrinsulfonamide in der informationsschicht
ITUD20130075A1 (it) * 2013-05-27 2014-11-28 Univ Degli Studi Udine Nuove pentafirine
EP2808328A1 (de) * 2013-05-27 2014-12-03 Universita' Degli Studi di Udine Pentaphyrine zur biomedizinischen Anwendungen

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TW544674B (en) 2003-08-01
US20030118937A1 (en) 2003-06-26
WO2002016144A1 (fr) 2002-02-28

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